Allylamine is a polymerizable amine which is well suited for the production of amine functional polymers. Some examples of its use are in the preparation of ion-exchange resins, preparation of polymeric paper additives for enhancing wet and dry strength in paper and the like. Current processes for production of these allylic amines are limited in practical conversion due to observed allylic alcohol polymerization at higher temperatures.
One of the classic routes to the production of allylic amines is by the reaction of allyl halide with ammonia or an amine. The reaction may take place either in the vapor or liquid phases. U.S. Pat. Nos. 2,216,548 and 3,175,009, provide exemplary process descriptions.
U.S. Pat. No. 4,417,074 discloses a process for the generation of allylic amines by the reaction of an allylic alcohol with ammonia or an organic amine in the presence of an effective amount of a phosphorous containing substance. Representative phosphoric containing compositions suited as catalysts include acidic metal phosphates such as boron phosphates, ferric phosphate, aluminum phosphate, phosphoric acid compounds, such as orthophosphoric acid, pyrophosphoric acid and alkyl and aryl substituted phosphorous and phosphoric acids such as methylphosphinic acid and so forth. For an orthophosphoric acid on silica catalyst, '074 shows a 11-23% conversion of allyl alcohol with ammonia at 81% selectivity to monoallylamine. Conditions were 300 psig and 277.degree. to about 320.degree. C.
A variety of amines have been prepared by the reaction of an alkyleneamine and a polyamine to produce alkylene amines such as triethylenetetramine and the like. Phosphorous catalysts have been widely used for the condensation reaction between the alkyleneamine and alkanolamine utilized in the reaction system. U.S. Pat. Nos. 4,983,736; 4,394,524; 4,605,770 are representative. The '770 patent discloses the use of metal acid phosphates including Group IIA and Group IIIB metal phosphates. Group IIA metals suggested include beryllium, magnesium, calcium, strontium, and barium. Group IIIB metals of which lanthanum is a preferred metal included scandium, yttrium and others as the rare earth lanthanide series.